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Chester VT Real Estate

Located in Windsor County, Chester is a wonderful New England town reminiscent of a bygone era. With architecture pre-dating the civil war, Chester is rich in history and beauty. Although historic, the quaint town is thriving with its unique markets, galleries, and restaurants that offer much to do. The town is also conveniently located close to Okemo Mountain and Mount Snow for those who enjoy outdoor recreation as well as within driving distance to Manchester, VT

Search the latest real estate in Chester, VT with Maple Sweet Real Estate. Find the right property for you from a variety of listings. To save your favorites, register with us and you can get email notifications when similar properties are posted. Already have an account with us? Log in here.

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134 Gold River Extension Chester VT 05143

Chester, VT134 Gold River Extension

Price$950,000The price has recently decreased

MLS Number 4837125

  • Commercial
  • Acreage 13.42

Rare opportunity with commercial/industrial zoning. 13+ acres of fully permitted subdividable lots. Property can be used in its entirety, or use what you need and market the permitted land parcels to others. Currently there are 6 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, and rail siding; 7544 sq ft open span, no ceilings, storage building; 3 additional storage buildings. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Large former ore shed with 7544 sq ft of open span. Multiple doors to access the building. Survey and permits in place for 7 lot subdivision of the industrial park. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Also offered separately (building lot, ore shed building, or garage/office/storage buildings). Video attached to the MLS.

Listed by Andy Paluch of TPW Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

141 Stage Road Chester VT 05143

Chester, VT141 Stage Road

Price$925,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4822981

  • Land
  • Area Near Skiing, Rural
  • Acreage 526.4
  • Utilities None
  • Zoning Residential

Don't miss the rare opportunity to own this spectacular acreage set between the rolling hills outside the beautiful villages of Chester and Grafton Vermont. The stunning 526 +/- acres has it all. Made up of 4 contiguous preexisting lots the parcel has road frontage on Stage Road in Chester giving multiple opportunities for a number of small subdivisions. Three lots also front onto route 35 between Chester and Grafton which includes two 70 +/- acres lots. There are also gravel deposits on the site which could be used to develop the logging trails further. If you have conservation on your mind the entire lot is enrolled in the Vermont Value use program which helps to keep the taxes low. The interior of the lot is mostly wooded and hosts a large open area for staging a logging operation. There are also a network of marked logging trails throughout the property making it easily accessible. The beautifully crafted ponds offer a welcome spot to take in the beauty of the landscape as well attracting all manner of wildlife. The seller will entertain selling individual lots separately. Whether you wish to develop or keep this pristine site as is you will find endless choices and opportunity for this very special place. Come see today!!

Listed by Daire Gibney of Barrett & Valley Associates,Inc/Chest

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

374 Richardson Road Chester VT 05143

Chester, VT374 Richardson Road

Price$749,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4908861

  • Residential Single Family
  • Bedrooms 3
  • Construction Existing
  • Square Feet 2,776
  • Bathroom 2

Gracefully settled between the villages of Chester and Londonderry, sits a Vermont Farmhouse at road's end, sited on eleven+ acres of wood'n meadow. Dotted with old stone walls, a wildlife pond and enchanting views. The setting is magical. A wide country porch invites rocking chairs and visitors while the screened area encourages outdoor entertaining much of the year. The vintage flavor is apparent throughout the home- opening panel doors with antique latches or stepping foot on wide wood floors milled from indigenous trees from decades ago. This location is central to recreating: ski, hike, snowmobile, swim, or enjoy our local restaurants, theater and shopping. A center island kitchen with breakfast nook overlooks the rolling meadows and glass doors allows life to spill over onto the porch, deck or firepit area. A traditional dining room, adjacent to the intimate living room, awaits memorable dinner parties. The great room's remarkable soaring ceiling creates a central gathering spot and includes a cast iron wood burning stove to warm by when winter is settling in and snow abounds . The main floor bedroom would also make a delightful home office overlooking the fields to the rear. Upstairs you'll find additional bedrooms including a large “beamed ceiling” primary and a fun multi-functional den/game room. Two sets of farmhouse stairs give easy access. If quiet and open and vintage is your desire..Look no further. Showings begin Thursday, May 12th. Owner is a licensed Realtor.

Listed by Lavinia Lee Brown and Nancy Jensen of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

835 Quarry Road Chester VT 05143

Chester, VT835 Quarry Road

Price$675,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 4908734

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,221
  • Construction Existing

If you are searching for the perfect Vermont setting for year round living and enjoyment look no further than "Hidden Meadow". Situated on a very private 23.52 acres you will find a home and property that has been lovingly cared for by its original owners. The house features a tile entry way that leads to a comfortable living room with vaulted ceilings, hardwood floors and a custom built modified Rumford Fireplace that will heat the room on those winter nights. The living room leads out to a screened in porch were you can relax, bird watch and look out over one of the most beautiful properties you will ever see. The rest of the main floor boasts an open kitchen with an island, ample counter and cabinet space, a formal dining room, 3 large bedrooms including a Master with private bath and a laundry room. The second floor space can used as a bedroom or a great home office with fiber optic internet. 2 car attached garage with heated workshop and a full basement offers a tremendous amount of storage. The property is special with a wealth of perennial gardens, mature abundantly producing blueberry bushes, lupine fields, custom stonework and steps. The large pond is 20 ft deep suitable for swimming and home to 100's of rainbow trout. The barn is suitable for animals with plenty of open pasture. The location is ideal, just 1 mile to the historic Chester Green and only minutes to the picturesque town of Grafton. Skiing and outdoor activities are also just minutes away.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

7 Pine View Drive Chester VT 05143

Chester, VT7 Pine View Drive

Price$580,000The price has recently decreased

MLS Number 4908570

  • Commercial
  • Year Built 2006
  • Acreage 1.56

Excellent opportunity presents itself with this outstanding commercial property located on Route 103 Chester. High volume traffic and exposure gives this property unlimited potential for the entrepreneur buyer. This exceptional post and beam structure sits on 1.56 acres and was built in 2006. Currently used as office space, it had been a retail shop, gallery and cafe in the past. Mixed use zoning allows for a future residential possibility. Over 3,000 usable square feet, ample parking, radiant heat, gorgeous tile flooring, natural wood beams. Town water and septic hooked up to the town line. Bring your vision and energy and create your dream.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$529,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4907617

  • Residential Single Family
  • Construction Existing
  • Bedrooms 9
  • Bathroom 9
  • Square Feet 5,242

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. Currently rented out as an extended stay rental and generating $8,800 monthly. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

266 Main Street Chester VT 05143

Chester, VT266 Main Street

Price$529,000The price has recently decreased

Active With Contract

MLS Number 4907618

  • Commercial
  • Year Built 1780
  • Acreage 0.75

This 1780's stunning yet quaint home in the heart of Chester and Southern Vermont is truly the ideal location for a spectacular private residence or successful hospitality business. Owned and operated with love this building has provided a warm welcome to all who have visited and have become enchanted with Vermont through the years. Currently rented out as an extended stay rental and generating $8,800 monthly. The period home with newly renovated 2 bedroom separate living quarters comes mostly furnished leaving you space to add your personal touches. The main floor is easily accessible with first floor accommodations for those needing to avoid stairs. Gracious rooms and cozy common areas invite you to relax in a central location allowing easy access exploring the surrounding Chester village and with mountains, lakes and streams all within short drive you will not lack options for fun and relaxation. Come see this charmer; you may want to stay awhile!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

74 Cobleigh Street Chester VT 05143

Chester, VT74 Cobleigh Street

Price$485,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4903312

  • Residential Single Family
  • Bedrooms 3
  • Square Feet 3,223
  • Construction Existing
  • Bathroom 3

One of the true gems of Chester. This circa 1850 home has been transformed over the years. It has the charm of the original farmhouse yet has the functionality of a newer home. You enter into a lovely enclosed screened in porch with newer windows which also serves as an entry mudroom. You'll step into a large living room with a woodburning stove with new stainless steel liner added when the chimney was rebuilt. Good sized kitchen has ample counter space and cabinets as well as an eat-in island with stools. The formal dining room has hardwood floors and a gorgeous bay window looking out to the front yard. First floor features an inviting family room with a wet bar, gas fireplace and access to the backyard patio. You'll also find on the main floor a bedroom, full bathroom, arts and crafts room and an amazing sunroom with brand new windows looking over the backyard. The upstairs features 2 bedrooms including an owners suite with a laundry room, dressing room, huge walk-in closet and a master bath with radiant heat and a double marble sink. There is also a second floor office for working at home. The property is special. It's beautifully landscaped all around with a vegetable garden bed, multiple outbuildings including a new 10X14 shed, small fish pond,fire pit and patio for endless hours of outdoor enjoyment. A 3 bay garage was also added in the past year. The house was recently painted and is move in ready. All this just a short distance to the historic town green.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1824 VT Route 11 East Chester VT 05143

Chester, VT1824 VT Route 11 East

Price$429,000The price has recently decreased

Active With Contract

MLS Number 4894211

  • Commercial
  • Year Built 1870
  • Acreage 2

Landscaping, hydroponics, hemp/cannabis, flowers/plants and wheat grass are just some of the indoor growing specialties this exciting property can support. Live comfortably in the attractively renovated vintage styled 2 bedroom, 2 bath converted schoolhouse while you master the art of growing. Work remotely and start a side online/home business that germinates your passion. Three enormous heated New England Style 96' x 30' greenhouse structures with automatic water system and dedicated artesian well will jump start your enterprise. Two additional greenhouse frames can be utilized. Steps away from your dwelling you can interact with customers and help beautify Vermont by getting involved with local beautification committees. Grow your own vegetables and practice sustainable living while hitting the slopes and enjoying all that Vermont has to offer. Cue the chickens... See mls #4894210

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1824 Vt Route 11 East Chester VT 05143

Chester, VT1824 Vt Route 11 East

Price$429,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 4894210

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,212

Grow, Play and Ski! Presenting the ideal property for a versatile home business. This completely remodeled 2 bedroom, 2 bath Chester country cape on 2 +/- acres awaits your entrepreneurial talents! The current owners had a seasonal, established Nursery business, successfully partnering with town beautification committees and supplying flowers and plants to local businesses. Major road frontage will attract business while the sounds of the babbling brook add to the setting of the house, artfully screened from the road. The lovely yard features stone walls, flower gardens, lovely flowering bushes and trees, and a delightful pond! Three 96' x 30' versatile, heated NE style greenhouses are ready for your horticultural ideas and are equipped with auto watering from a dedicated artesian well. The open concept design of the house has been thoughtfully updated with artisan flair and architectural details. The first floor living area includes stainless steel appliances, wood stove and full bath with vintage clawfoot tub and stackable frontloading washer/dryer. The 2nd floor features 2 large bedrooms with closets and storage space, vaulted ceilings, new carpeting, a full bath and balcony. Dine and relax outside in 3 seasons on the private deck. Whether your dreams are of sustainable living, raising chickens, nursery/landscaping or other indoor growing pursuits, work remotely and customize the template of this unique property to enhance your VT lifestyle. See mls # 4894211

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

134 Gold River Extension Chester VT 05143

Chester, VT134 Gold River Extension

Price$425,000The price has recently decreased

MLS Number 4837151

  • Commercial
  • Acreage 2.49

Rare opportunity with commercial/industrial zoning. 2.49 acres that is fully permitted. Property can be used as one business spot, or share the office building with another business. Currently there are 3 buildings onsite to include: 1792 sq ft office building; 3364 sq ft garage building with heat, loading dock, office, and rail siding; plus an additional 1500 sq ft storage building. Property includes an owned rail siding for direct shipment possibilities. Highway access is on Route 11 East, 3/10's of a mile from Route 103, and 9 miles to Route 91, exit 6. Office building has center entry and two administration wings, could be used by two or more businesses. Fiber-optic internet is on site. Garage building is currently used for service of trucking and excavation equipment and includes office area. This building has loading dock and direct access to rail siding. Common rail siding to be maintained for all. Currently there is a tenant in the office building. Also available separately (building lots, ore shed building, or the entire parcel-see MLS 4837125). Video attached to the MLS.

Listed by Andy Paluch of TPW Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1377 VTRT 103 Chester VT 05143

Chester, VT1377 VTRT 103

Price$400,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 4871606

  • Multifamily
  • Bathroom 2
  • Units 2
  • Square Feet 2,280
  • Acreage 3

Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business.

Listed by Michael England of Michael England Real Estate

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 5.25% last updated on 2022-05-19

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity

Copyright 2022 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated May 24, 2022.

 

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